Caribbean yacht charters

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Sailing experience level

Sailing in the Caribbean

On a Caribbean sailing vacation you'll experience your nautical dreams in a unique and thrilling way.  Set sail aboard your private charter yacht from one of seven island bases, each with their distinct history, delicious cuisine and culture waiting to be discovered. 

Whether you want calm, protected waters and short island hops or exhilarating blue water passages, the Caribbean is one of the most exciting sailing vacations you can experience.

More than 5,000 islands, reefs and cays make the Caribbean a picture-perfect paradise for sailors at any experience level. You'll enjoy easy line-of-sight navigation, deep water passages and lively island-hopping from one charming harbor to the next aboard your own monohull or catamaran Caribbean charter.

Destinations in the Caribbean

The British Virgin Islands

  • Visit a real-life Treasure Island
  • Steady trade winds, calm currents
  • World-famous yachting destinations
Flotillas Experience level 1
Explore The British Virgin Islands
The Bahamas

The Bahamas

  • Beautiful beaches
  • Famous wreck dive spots
  • Blissed-out year-round sailing
Experience level 2
Explore The Bahamas

St. Martin

  • Blue water and coastal sailing
  • World-class diving and snorkeling
  • Glamorous resorts and laid-back beaches
Experience level 2-3
Explore St. Martin
Antigua

Antigua

  • Excellent wreck and reef diving
  • Blue water sailing in steady trade winds
  • A stunning beach for each day of the year
Experience level 2
Explore Antigua

Belize

  • Sheltered sailing within a barrier reef
  • Consistent coastal trade winds to exploit
  • Incredible rainforests and Mayan ruins
Experience level 3 ICC RYA
Explore Belize
Grenada

Grenada

  • Exciting blue water sailing
  • Warm, yearlong trade winds
  • Excellent diving and snorkeling
Experience level 3
Explore Grenada
St. Lucia

St. Lucia

  • Year-round trade winds
  • Unique, delicious local cuisine
  • Stunning mountainous, rainforest isle
Experience level 3
Explore St. Lucia
Father And Sons In Bahamas

Exumas, The Bahamas

  • Onshore and offshore experiences
  • Protected marine parks in the world
  • World-famous swimming pigs
Experience level 3
Explore Exumas, The Bahamas
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Charter types

You can choose to charter your private yacht as the Captain and set sail for your dream Caribbean island destinations or hire an expert Skipper for your entire trip or for just a day or two.  If social sailing is your scene, opt for a Flotilla eperience.

Caribbean bareboat charter vacations

Set sail on a bareboat charter in the Caribbean to enjoy your experience from the helm.  Take your time and sail at your own pace.  You’ll find a spectacular balance of easy line-of-sight sailing and adventurous open water thrills for your perfect sailing vacation.

Skippered Caribbean charter vacations

skippered charter vacation in the Caribbean lets you have the best of both worlds. Your qualified skipper will show you the spectacular sights of the Caribbean at the pace you choose to see them while you relax away from the helm.

Caribbean flotilla vacations

On a Caribbean flotilla vacation, you'll find yourself sailing through the day and dropping anchor amid the magical cays, bays, and harbors with your flotilla.  Your evenings will be enjoyed with your flotilla sailing companions over dinner ashore or drinking rum punch on the deck of your yacht.